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A podcast that explores how AI is transforming careers, businesses, and industries. Hosts Greg Boone and Erica Rooney deliver real-world use cases and actionable AI strategies to help professionals stay ahead of the curve.
Ashley Gross: This is like any
other tool in your toolkit.
You're bringing a specific
level of expertise from all of
your experience and all of your
conversations that you've ever had.
So applying what you know to make it
better with AI or to enhance it with AI
is really the only way to think about it.
But if you don't have anything,
like if you're in a role right
now where you're like, I hate
this role, get outta that role.
Go figure out something that you're
passionate about and then add AI to it.
Greg Boone: AI isn't the future.
It's now.
And whether you're in hr, sales,
operations, or leadership, the
choices you make today will determine
whether you thrive or get left behind.
Erica Rooney: Today's guest is
living proof that AI isn't just
for techies, it's for trailblazers.
Meet Ashley Gross founder and
Cee O of AI Workforce Alliance.
When generative AI first hit
the scene, y'all, Ashley slashed
her work week from 40 hours to
15 without sacrificing results.
Since then, she's helped companies
generate over 100 million in pipeline,
built the AI impact alignment
method, and become the go-to expert.
In workforce AI strategy.
You've seen her in Forbes, Microsoft,
and on stages around the world.
Y'all, let's dive in with the
brilliant and incredible Ashley Gross.
Ashley, how are you?
Ashley Gross: I'm great.
Thank you so much.
That was a lovely intro.
Erica Rooney: You know,
we try to keep it snazzy.
We try to keep it snappy, but I
would love to just dive in and tell
us all about your journey into AI
Ashley Gross: and how that started.
Erica Rooney: Yeah,
Ashley Gross: honestly, it's
just a humble beginning.
I found out I was gonna be a mom in 2020,
and very naively I went to my employer.
I don't really know what I was expecting.
I think looking back maybe like
a Target gift card and like a
congratulations card, and instead they
were like, Hey, that's amazing, but
we don't offer maternity leave here.
And so I was like, oh, okay.
I'm looking at my marketing tech stack.
I've been a marketer for 10 years, and
I quickly realized there's no scenario
where any of these tools are going to.
Give me back more time
to spend with a newborn.
And so I started doing a lot of research.
I'm a big podcast and newsletter
gal, and I learned about a tool
called Jasper and I started using it
and was able to consolidate my work
week, and that made for a much easier
experience as a new mom, obviously.
And once I was able to.
Consolidate that work week.
I realized I was spending a lot of my
work day doing tasks I hated doing.
Like we always talk about like the role
we want or how much money we want, but
we never have a conversation about the
tasks we have to do every single day
and whether or not we like them, I.
So I was like, okay, there's,
there's no scenario where I'm the
only one that feels like this.
And so I started talking to the
CMO at the enterprise I worked for,
and sharing some of the playbooks
and the prompts that I was using.
And she was like, okay, we want you
to deploy this in the marketing org.
And then the product org and then sales.
And that's when I first
saw a tangible metric.
We overachieved our pipeline by 25
million just within three months of
taking my individual playbooks and
prompts and giving them to teams.
And this was early 2022
before CHA GBT had launched.
Cha GBT launched around
March of 2022, I believe.
And so really that was, I mean,
it was a wild West time, even back
then, but nobody was able to really
put ROI metrics on AI adoption.
And so the fact that I was able to
do that and I had a playbook and
prompts and it worked in different
departments, I was like, okay, freeze.
I love being a marketer, but
I wanna double down on this.
And that's what really gave me
the courage to go back to school.
You know, learn to be a little bit
more technical, learn to code, and
lean into just being a student again,
because I didn't feel silly, like
I think before learning AI and, and
seeing tangible metrics, I would've
been like, why would I learn to code?
Like, that's not in my ballpark,
that's not in my wheelhouse.
But I was like, no, like I a
hundred percent should do this.
I've seen the ROI, I'm gonna double down
and figure this out because once you
optimize these tools, then you start to
kind of like unleash this new level of
optimization where you're like, well, I
like this tools user experience, but I
like the back end of this tool better.
So then I just started building my
own solutions and that led to me
starting my own agency and being able
to implement AI into enterprises today.
Erica Rooney: Oh my gosh.
I love that story.
And the fact that you did all of
that in like what, just three years?
It's insane.
Yes, it's insane.
But tell me
Ashley Gross: about AI
Erica Rooney: Workforce Alliance.
Ashley Gross: Yeah, so AI Workforce
Alliance is for enterprises.
Um, this agency of mine,
we have a framework.
So we do everything from those
initial conversations with, um,
C-Suite staff and, and founders of,
okay, you wanna start using AI tools.
You don't have AI tools that are
accessible to your employees.
Like, where do you start?
So we do everything from building
them a roadmap to helping them vet
vendors safely and giving them guides
to actually deploying and doing
enablement sessions with those tools.
We start there, but then we take them on
this evolution naturally of, okay, there's
going to be certain AI tools that you
want to bring on and certain vendors that
do great jobs, but to a certain degree
there's a level of risk and autonomy.
Perhaps you wanna start building
these solutions in-house so the
data never leaves your environment.
So that's when we start to build
some of the marketing automations and
some of the marketing agents for them
in-house, and then we maintain them.
So it's like a full lifecycle, but if
you think about it, it makes sense.
I don't think that anybody, I. Can
safely and accurately build a strategy
for companies without building the
solutions and or maintaining them.
'cause it's almost like you're just
going in there and like hyping them
up and saying like, you can do this.
Your employees will be this
much more productive, you'll
make this much more money.
Here's a playbook.
And then like you bounce.
And that didn't make sense to me.
So I wanted something
that felt more holistic.
I love that.
And I think.
Erica Rooney: With AI right now and
all of the things that are going
on, people really need someone to
guide them because they're, they're
facing experimentation, fatigue.
There's too many tools out there.
There's too many options.
What does my tech stack need to look like?
So I'd love to hear from you.
Why do you think that so many companies
get stuck running all of these different
AI pilots that never really stick?
Ashley Gross: I think part
of it is fear paralysis.
So there's lots of companies that
have executives saying like, we're
gonna be AI enabled, go experiment.
But they don't have tools that
they're giving employees access to.
They don't have a budget for it,
they don't have resources for it.
They might not even have like a Slack
or a teams channel showing like wins.
So like it's not normalizing
it in the culture.
If your executives have fear that is
going, that sentiment is going to flow
down to the rest of the staff and like
they're not gonna feel safe using it
because they have no idea how to safely.
I think that's part of it.
And then I think the other part of it is.
It's one thing to be an experimenter,
but it's a whole other thing to
be responsible for these tools.
And so when I rolled this out back
in 2022, you know, it might not
have been coming outta my budget.
The tools might have been coming
outta the CMOs budget, but InfoSec,
privacy, security, they were asking
all the questions and I had to
have answers for all of those.
And so when you have that level
of visibility and pressure and
the dependency of this being a
success, you act differently.
And I think that's an experience that.
You know, you can read about this
all day long in books, but like until
you do it, you're just never gonna
have all the cards and the context,
because AI is an emotional change.
Like that's the change management.
It's not technical, it's emotional, and.
So I think just having that lens and
having actually done all of that and
had all the pressure, I'm able to see
from the executive's perspectives,
but also the employee's perspectives,
mid-level, entry-level employees and
what they're thinking and have those
emotional, uh, intelligent conversations
baked into the planning and the
rollouts and the experimentation.
'cause you can't have safe experimentation
without holding space for the
questions that the staff wants to ask.
Greg Boone: Yeah.
I mean, I think that's a,
uh, an excellent point.
We, you know, talk a lot about at
Walk West, I would say, you know,
you gotta make sure that whenever
we're rolling out ai, whether it's
internally or for our clients, right?
I was like, look, you wanna
focus on three things, right?
Making sure it's safe, secure,
and sustainable, right.
To your point.
Yes.
And safe being things like brand
safety, psychological safety,
giving them a safe space to play.
And as Cee o and Erica is our
chief people Officer, we're like.
We know that this is a
change management game.
This is not just a technical, you
know, conversation we're having.
So we go through the entry point of,
we start from like an HR and a people
and employee experience perspective.
And I say, look.
If you want people to adopt this,
and I would love your take on this.
I always say, I say, this is what we do.
We make it personal, we make it
fun, and we make it safe, right?
We don't care if you mess up.
We don't care if you do X, y, and
Z. We do it in a very contained
kind of environment, but we've split
up the entire company into groups.
We've all, uh, I think it's like, you
know, five or six different teams.
We have a certification
conversation going.
Right now we have a hashtag
that's going on LinkedIn.
So when people are posting about it,
we're just trying to make it fun.
But I always tell folks I'm like.
Just because you have some
business idea, to your point,
the boards wanna talk about it.
Executive teams, I say, but no one's gonna
give two shits about your business outcome
if you have not made it personal to them.
How do they individually get more
productivity gains out of this?
And so we're taking a very personal
approach to this and saying, this is
how it's gonna help you in your role.
This is how it's gonna help your team.
This is how it's gonna
help the organization.
We start to stair step.
Up from that perspective, but we do
believe it's highly a change management
situation, and my background is in
computer science, so I went computer
science, then marketing and business.
And I think you went
the opposite direction.
Yes.
Well, we got to the same point.
Ashley Gross: Exactly.
That's all that matters.
You have the best
Erica Rooney: of both
Ashley Gross: worlds,
Greg Boone: right?
Erica Rooney: Oh my goodness.
Tell us about your AI impact alignment
method and how that really helps
teams move from the experimentation
phase into the execution phase.
Ashley Gross: Yeah.
Greg's tee up was perfect for
this, so I would say it's.
Starting with a problem.
So in a discovery call that I have,
when there's early indicators that
they're interested in working with
me in that discovery call, there's
rules, like there's pre-homework
to do before a discovery call.
So this is not like a discovery
call where you know it's all on
the vendor and there's magic, and
I have to like show you all these.
Things and wow you.
It's like, no.
If you're ready for a discovery
call, you're going to pay and
you're gonna have pre-homework.
And if you don't complete
that pre-homework, we're
not gonna have this call.
Because I need to know that you
are holding yourself accountable.
Mm-hmm.
And you're actually ready
for this conversation.
And part of that pre-homework
is what is the biggest problem
that your organization is facing?
And I give this to founders and C-Suite
members, depending on who brings me in.
So if it's marketing, it goes to the
CMO, sometimes like the next level down.
So director, um.
Perhaps with like digital
marketing or demand generation,
and I say like, pick a problem.
Like what is the biggest problem?
Would you say it's lack
of clean and rich data?
Lack of insight in the customer
journey or slow sales cycles.
And I walk them through this workflow
of, once you choose a problem, tell
me three ways and past roles where you
have solved part or all of this problem.
So now I'm getting them to identify
a problem that is a very big pain
point across the whole organization
and not just specific to them.
So I'm avoiding that silo of like,
well, marketing's winning, but sales
isn't like, no, we're not doing that.
And then once they diagnose the
problem, it's like, okay, remember
how you've solved this in past lives?
'cause we never give each other
like enough credit for what we're
doing in our accomplishments.
So it's like a reflection.
And then going into the call I say,
okay, look, you said slow sales
cycles was your biggest problem.
That's what I'm hearing.
The Cee o coming back to you
saying, we have to fix this for,
you've given me a timeline of,
of how fast you need to fix this.
And you've given me ways and past roles.
That you've achieved some level
of success solving this problem.
Here are the use cases that all bubble
up to solving that problem that are gonna
be deployed as part of this package.
And we're gonna choose teams from
different members of marketing or
different members of sales to be in the
experimentation groups that are going
to work for these individual use cases.
That all bubble up again
to solving that problem.
And I give them templates with qualitative
metrics and quantitative metrics.
I have a very, you know, simple but.
Consistent template for how to
measure ROI and success even when
they're experimenting initially.
So then once we see early success
in those proof of concepts, then
we take them to a pilot project.
And so if the experimentation group
was just one team, like let's just
say it's like paid ads team or
social media team, that's when we.
Document the success and we bring it to
the other teams in marketing and say like,
we want you to try to replicate this.
Once it's successful, we scale it out.
We document it, it lives on Confluence
or wherever their central knowledge
base is, and we have announcements.
Hey, here's how this
worked, here's what we did.
This is a playbook now.
So that's, that's truly like, that's it.
That's my secret sauce.
That's my playbook.
It's more so just.
I'm not going to make them do two
things that they've never done.
I'm not gonna make them experiment
with this tool and try to derive
value and measure ROI when
they've never done this before.
Like I'm gonna do that for them and
guide them in a way of thinking about it.
And I almost wanna say it's like.
When you first learn to write a
resume, as cheesy as it sounds like
your first resume, thank God, and
I don't have mine 'cause I would be
mortified, but like on your first
resume, you're like, I served ice cream.
I smiled at customers
like I opened on time.
Right?
And then when you learn how to articulate
what you're doing, you start putting
quantitative, qualitative metrics
there because you learn quickly.
What you do matters, but how you
communicate what you do matters more.
And that's what we do with
the Alignment framework.
Erica Rooney: You talked about the
different metrics for success in
experimentation and I would love to
dive a little bit deeper in that.
Yeah.
Because I'm not sure that
everybody understands like what
you can actually quantify there.
Ashley Gross: So with a pilot it,
it differs because with a pilot,
I really want everyone to just.
Make sure, or let me go back
actually with a proof of concept.
I want to enable experimentation and give
them one hypothesis and one objective.
So if the use case, for example,
is, um, using copilot to, um.
Reschedule my workday and prep me
for calls Is saving me is going
to save me five hours a day.
That's it.
Like that's the hypothesis.
The objective is to at least save five
hours a day in prep time for calls.
So then the metric for
that would be, did it work?
Yes or no?
Like were you able to accomplish
it if you accomplish more or
less, like put that number down.
That's proof of concept.
'cause it's really getting
people to go back from, it's
okay not to know everything.
That's the point of experimentation.
You're safe here.
Just like, do you think you can do this?
Did you do it?
Write it down.
And then when we move into a pilot that's
more about what are the efficiency gains
like, what are the productivity gains?
Um, were you able to, as a department
or as a team, take that same use
case of one individual saving
five hours a day and multiply it
by your headcount for your team?
What does that number look like?
Because I guarantee you, if it worked
for one person, then we're looking
at a whole team, they're probably
saving 30 hours a week just in
prepping for calls and looking at
their day and planning their day.
That's a huge efficiency gain.
So that would be the metric.
And then when we scale it out, that's
when we turn it into like revenue.
So how much time are we actually saving?
From an employee perspective, like what
are we paying these employees per hour
and how many hours are they saving,
prepping for meetings with copilot,
let's put that into revenue metrics.
And I wanna look at that because as
you scale something out, leadership's
gonna wanna know, they're gonna wanna
have eyes on, and inevitably you
have to bring it back to revenue.
But it shouldn't be brought in so
early that people are worried that
they're experimenting wrong because
they can't tie it to revenue.
Mm-hmm.
So there's a time and place.
Erica Rooney: I love that.
That is incredible.
Any questions?
Greg Boone: Oh, I have a lot of questions.
Lot.
I was gonna say, lot comments.
Erica Rooney: I see you.
Go ahead.
Have a lot of thoughts.
Dive in, dive in.
Greg Boone: Look.
'cause you know, uh, as we talked,
um, off camera before we, we started
this, I, I already told Ashley I
was a fan because I've listened
to her on other podcast, right.
Talk about, you know,
some of these things.
And I, I'm fully aligned with
kind of the, the strategy.
Uh, you know, one of the things
I've listened to you before talk
about was the outcomes, right?
And focusing on, on the outcomes.
I'm always a big, uh.
Start with the end in mind type of person.
Right?
And, uh, anytime I do these types of
strategy, uh, sessions for the last
15 years, I always tell folks it's
people, process platforms in that order.
Always.
It's like, you guys wanna jump to
the technology and the platform.
You have a change
management, uh, problem here.
You know, one of the things that, um,
the team here at Walk West knows about
me is that I take a lot of these courses.
Right.
I kind of nerd out.
I've, I got a ton of certifications,
but one of the more impactful ones
speaking to this change management
is earlier this year I took one, um,
leading, uh, leading in the age of, uh,
AI at MIT and it was all about how we're
transforming Walk West to be this more
modernized AI first type of organization.
And I clearly did something correct
'cause now they're using that video of
my case study on current, uh, students.
So, you know, uh, shout out to MIT.
They did a great job.
But one of the things they talk
about, uh, a lot of times is creating
that safe environment, but then
focusing more, they talk about
this forgiveness continuum, right?
And focusing on internal
versus external, right?
So when you're gonna pilot, don't
pilot on your end customers,
because from a forgiveness continual
perspective, uh, there's gonna be some
challenges if things go wrong, right?
And that's where, and so I think sometimes
to bring it back to what you were saying.
When I hear revenue, I'm good because
I'm a Cee o. Most employees though, you
know, they get that heart palpation.
They say they get scared.
They're like, when you start talking
about revenue, like whoa, whoa, whoa.
The game has changed.
I thought we were talking
about productivity for me.
Erica Rooney: Yes.
Greg Boone: Now you're talking
about the revenue side.
So one of the things that's top of
mind for me, going back to that, uh,
that course at MIT, my problem set.
One of the things, and I've heard
you talk about this and when we
talk about the time equation, is.
I wanna bring, when you talk about
revenue, what about the hourly rates?
Right?
What about like, how are, how should
we be thinking about this now?
Because I keep telling folks like, I
can do a lot more and a lot less time
right now that could impact your revenue.
I hear a lot of the, the publicist, WPP
folks that are publicly traded talking
about, you know, the impact of my
revenue goes down, but my profitability.
But the streets don't care about that.
Right?
So I want your take on this like,
'cause you, you talked about
flipping that time equation.
Yes.
What do we do now?
Absolutely.
Ashley Gross: Um, as far as like how they
go about it or like the why behind it?
Greg Boone: Well, if you're
justifying ROI, right?
Mm-hmm.
And we're acknowledging that
we can do things faster, right?
Yes.
As, as we get greater market
sophistication, the consumers are
going to expect us to do things faster.
Yes.
And then there's this natural,
you know, all, it's not just
change management internally.
Part of what Erica and I are trying to do,
we're trying to change the world because
people are trying to sell things that
the consumers are not ready to actually.
Consume.
Right, right.
And so if the expectation is,
let's take about, let's talk about
like legal professions, right?
If I can get something faster and
you used to charge me an hourly
rate, should I not get it cheaper?
Ashley Gross: Okay, great question, right?
So how
Greg Boone: do you define ROI
when things are expected to be
cheaper is, I guess my point.
Ashley Gross: So here's my pitch whenever
this conversation comes up, because I
haven't been charging hourly for the last
year and a half since I started my agency.
I
Greg Boone: heard you and I love that.
Ashley Gross: I'm making way more money.
Um, so like it, it works.
And the reason why I kind of push
this narrative is if you hire someone
that is $50 an hour and you give them
a three month contract to complete
something and they complete it in
less time, are you going to pay them
less money because they completed it?
Less time.
So ultimately it's better for you
because you have results faster.
Wouldn't you wanna pay them based on the
outcome, like the value of the quality?
Instead of being in a time
bind and expecting something
in a certain amount of time?
We almost created this internal laziness.
To a certain degree where we are
telling people that they're busy bees.
Yeah.
And they're getting charged per hour and
compensated for the work they're doing.
And we just want them to keep working
when in reality, there's no incentive
for them to do better jobs at the
tasks they're doing because they know
that they're getting paid on the hour.
But if they're getting paid on
the outcome, they're going to
approach every task differently.
They're not gonna just do something
for the sake of doing it because
they've done it this way 10 years.
They're going to break that.
Toxic mentality of like, well,
it's always been done this way, and
they're gonna think, how can I do
this better so I can do it faster?
Because I wanna be charged
based on the outcome I provide.
And that's how you change a culture
internally, because if people, which
this doesn't happen, by the way, this
is part of the training that I provide,
if people knew how much time they were
spending on tasks, like at the end of
every week I have an extension that
tells me how long I'm spending per task.
And then it's actually bucketed
into busy work or strategic work.
When I did this practice back in
2020, I was mind blown that the
strategic work was less than five
hours a week because I was spending
the rest of the time on busy work.
And at the time, the
end goal for me was CMO.
I would've never made it to
CMO within the next five years.
Ever had I not just taken a minute
to see where that time was being
spent, because those busy work tasks,
they're not gonna get me in boardrooms.
They're not gonna help me practice
talking to leadership or having
conversations or negotiating.
So I'm not gonna be prepared for
those higher level roles, those
bonuses, those promotions that I want.
So.
I think that's really like the
end goal is, yeah, like consumers
already expect these things.
Like when you get on Netflix, you
have an a la carte buffet style of
movies and TV shows based on your
personal preferences, so you don't
even have to scroll or think about it.
If you go to Amazon or any other
provider, you probably don't spend
nearly as much time on there.
Because you have to look, so
like from a consumer perspective,
we've already seen this.
They want instant gratification,
they want instant value.
So why haven't we changed our
internal culture to match that as
well and provide that value faster?
It's like this misalignment that's
existed for years and I think AI is
the perfect tool and it's a really
good timing in the market to like
kind of connect these two pieces.
Greg Boone: Yeah, it's
really exposed the, uh.
I always call it like that
accelerated time to value, right?
And so to your point, if I
can do it faster, right, then
you get that value sooner.
Wouldn't you like that more
than to simply wait, right?
Just for the sake of, of waiting.
Right.
And it is, and and to your point, whether
it's Netflix or Amazon, people are
already, people say, well, I don't use ai.
I was like, you don't
know that you're using ai.
Right?
AI is using you like whether you
have acknowledged that or not.
And so I think that, I mean,
that is, is, is so spot on.
I think they, we talk about
the productivity crisis.
I, a lot of times I, I frame
things as kind of two ways.
There's a lead flow crisis that
we can get to a little bit later.
I've been trying to talk to folks for.
Nine months now about, I always say,
I said, may of 2024, Google turned
the lights off and a lot of small
businesses, when they went to AI
overview and nobody would pay attention.
Right.
And I was just like, people would
look at me like I had two heads.
I was like, I don't understand
if why you don't get this.
Right.
Like pretty, as we talk about this
on the podcast all the time, as as
humans, we search for answers not links.
Right?
Right.
And so I talk about the.
Lead flow crisis.
And together when we're talking
to rooms, we talk about the
productivity crisis, right?
That you're describing.
And there's, you know, uh, there's
evidence that the average knowledge worker
spends greater than 50% of their work week
either searching for things to do their
job, copying and pasting or reformatting
data over 50% of your work week.
Like, I don't know who signed up for that.
I certainly, as a Cee OI
wasn't hiring for that.
Ashley Gross: Right.
Greg Boone: That's the reality of,
to your point, and someone, um,
recently said, part of it, I think
is the challenge of like how the, how
the, the economy has been built over
the last, you know, 150 years and
this kind of factory worker mindset.
So to your point, everyone from,
from the business community to the
educational community has been in
this kind of siloed kind of factory.
You do this thing, you hand it to this
person, it should take x amount of time.
Right?
Yes.
And then we started, you know, 20
years ago with more automation tools.
Now AI has accelerated that to a
whole new level, and the consumer has
already expected much faster than the
business community can turn it around.
So it's up to folks like
you and I and Erica.
We're trying to educate folks, but
the change management is hard, right?
Absolutely.
So this is why I have
great people like you.
Erica,
Erica Rooney: I wanna know for
the people, what are the skills
that matter most right now?
Like what should they be doing?
We're doing it for the
Greg Boone: people.
Erica Rooney: We're
doing it for the people.
All right, let's do it for the people.
You took like 57 courses
between the two of you.
Yeah, but we're doing it for the people.
We're doing it for the people.
All right.
Ashley Gross: Um, okay, so
skills, I would say the avail
availability of yourself to just, um.
Communicate really well and
always improve the communication.
That's the thing.
Um, the humbleness or ability to humble
yourself and kind of erase this mindset
that you're never gonna be an expert
like that should not be the end goal.
'cause no one's actually an expert.
And when someone tells me they're
an expert, it's the biggest
red flag to me because it means
that they want to stop learning.
Like they feel personally, like
they know everything and they
don't need to know anymore.
And to me.
That is the biggest red flag
because that tells me that you're
not willing to be a student.
You don't want to learn a different way
of doing things because you're hung up on
the idea that your way is the best way.
Yes.
And that's never the truth.
Like we always have to adapt and
be flexible, and that's what you're
gonna see the most success in.
I would also say along that line, uh.
Your emotional regulation ability,
because this is emotional and you have
to hold space for some folks that are
going to be on different wavelengths.
Some people are going to want
to have conversations about will
this replace me while others are
like, I want 10 more AI tools.
'cause I just found ROI and I'm able to
bring in so much more revenue for this
business and I'm like ready to fly.
So like you have to add this emotional
regulation of everyone's at a
different place and like you gotta
be okay with that and learn how to
navigate those certain situations.
And then I would also just say like
ongoing learning in your domain,
because this is just another tool.
This is just like Google, this
is like any other tool in your
toolkit, you're bringing a specific.
Level of expertise from all of
your experience and all of your
conversations that you've ever had.
So applying what you know to make it
better with AI or to enhance it with AI
is really the only way to think about it.
But if you don't have anything,
like if you're in a role right
now where you're like, I hate
this role, get outta that role.
Go figure out something that you're
passionate about and then add AI to it.
'cause AI is an amplifier.
So if you are trying to.
Have it fill in a gap that you don't
know if that's, you know, a knowledge gap
that you're trying to have AI fill, or if
it's, you know, I would just say like, um.
Like a passionate gap.
Like you don't feel
passionate about your work.
Like AI's never going to do that.
It's an amplifier and enhancer.
So you already have to know what
you like doing and you have to be
willing to be like a specialist
when it comes to that industry.
Like if you're in marketing, the first
thing you should always do is when
you're, you about to start working for a
company or you're a consultant and you're
about to start, you know, onboarding a
company, um, go to their website and put
yourself in the shoes of their users.
Go fill out their lead generation magnets.
Go click on all their links like.
Even LinkedIn on a daily basis has a
link that's broken or a, a non-mobile
friendly, you know, formatting.
So like go back to the basics and always
try to be like a specialist in your
field and never lose that side of mind.
Erica Rooney: I love that.
The first three things you
said were all soft skills.
Oh yeah.
It wasn't like make sure you know how
to do prompt engineering or like dive
into, it was not a technical thing and
I wanted to really point that out so
the listeners could hear like, this
is not about being a technical person.
This is about the human side of it,
the communication, the humbleness.
So I thought that was.
Chef's kiss the, the HR heart
in me is very happy with that.
But what I would love to ask you
is like, how do leaders create a
culture that can really welcome ai?
And we touched a little bit about
making it safe, but how do you really
get that in ingrained in the culture?
Ashley Gross: Yeah, so
it starts with the top.
So I would say benchmark
yourself as an executive.
Do you have fear paralysis?
And if you do identify the reason behind
it, are you scared that if you don't roll
out ai, that it's your job on the line?
Like, are you feeling pressure
from the board or the founder?
Is that the fear paralysis or is it you
don't know what to do and you're just in
this like freeze mode of, I don't know
what I'm gonna do, so I'm just gonna hope
that the rest of the org figures it out.
Blessings to all of you.
Like which identify the fear paralysis.
'cause fear is totally normal
and it exists everywhere and
everyone has a certain level of it.
But identify it, put it
on paper and identify it.
And then I would say from there, make
sure as an executive you are asking
for the resources that you need,
whether it's taking some certifications
or going to in-person conferences
to absorb that type of information.
Um.
Based on your role and like based
on what the initiative is that
you're trying to drive with ai.
And then once you feel comfortable,
you should start having conversations.
But don't jump the gun and try to have
conversations and push AI initiatives
if you don't feel comfortable because
everyone's going to feel that.
Um, you don't have to say anything.
People know and they can sense fear.
So once you have.
A little bit more confidence.
You have the resources as
an executive that you need.
The way that you create safe spaces
is removing yourself because you were
taught and you worked your way up from
the bottom to an executive by doing the
same thing over and over and over again.
So you've got a little bit of a
prejudice, you've got some bias
in how things should be run.
You're not the best at
experimentation for the sole
purpose of making the organization
safe, and that is a spicy take.
So I'm sure the listeners have lots of
thoughts, but just hear me out here.
You are not going to feel comfortable
if your boss is like in the Slack
channel with you saying like,
what did you do with AI this week?
Like, how did you experiment safely?
You immediately are going to feel
pressure and you're gonna be like,
well, I did save five hours yesterday.
But like, that wasn't a great use case.
And like, I don't think that
he or she cares about that.
So like I'm not gonna share that win.
It's compounded growth, so remove
yourself, take the pressure off of
the rest of the teams and split them
up into groups like create working
groups for activation and experience
and content, and then put different
team members that aren't used to
working together in those groups.
And if it has to be asynchronous
and not a virtual call.
You have them share,
you know, weekly wins.
You can do this very easily with bots and
slack and teams so that like every week
a bot, you know, in the Slack channel for
each working groups is like, what's a win?
What's a prompt you used just to keep
consistency and keep people knowledge
sharing and building that repository.
But it's in a safe place, it's
low level pressure and you get
them to see that anyone can do it.
Um, and then you also back that, right?
So.
You don't know what's gonna
motivate every single employee.
Like a good manager should know
their team and they should know
what motivates their employees and
what their goals for growth are.
But let's be honest, especially at an
enterprise level, that's not possible.
Especially if like one person's
managing, you know, 50 plus people.
So put it, put some
money and put some words.
And a motivation behind what
you're trying to push out.
If bonuses are coming up, if
promotions are coming up, make
experimentation with generative ai.
One of the core pillars for asking
for promotion or asking for a bonus,
um, bucket it with learning and
development initiatives, like make it.
Make such clear sense to any employee
that regardless of who that employee is
or what department they're sitting in,
they understand that this organization
is pushing ai and if they do this, this
goes towards their growth at the company.
That's how you make it personal and safe.
Greg Boone: Yeah, I mean, uh, I got
a lot of great thoughts on that.
I don't know.
They're great, but they're, they're, uh.
Personal feelings, but one of the
things I was most excited about a
couple weeks ago, I was, um, I got
in, invited out to a HubSpot, uh,
AI summit out in San Francisco, and
Databricks conference was also going on.
And at the same time, our team, Erica and
others were doing some internal training.
And one of the things I was talking
to our, our chairman about, I was most
impressed with, I didn't have to be.
There and it created a more safe space for
people to play around with these things.
Right.
I remember back in the day, we had
some colleagues in our previous
business that we were together.
You know, something would go bad and
we would have leaders that would say,
I'm just gonna sit in the middle of
everyone every day and work with.
It's like, yeah, I don't think
that's actually gonna help.
I think it's gonna actually
make things a lot worse.
Yeah.
Right.
And because people need that
ability to fail and not seek,
I mean that power dynamic.
Exists, right?
And then you, you add in AI and
there's like, whether you call it a
fear paralysis or some folks will say
loss aversion or future shock, right?
Several, uh, I guess about almost
two months ago now, I was on a panel
at the, uh, American, uh, marketing
Association in Chicago, uh, event.
I remember the, the Cee o Benny, uh,
was asking me on his podcast before
the panel, he said, Greg, gimme one
word that you would give, you know,
marketers out there, um, on what
they need to be doing right now.
I said, first of all, you're asking a
marketer say something, one word, right?
Okay.
Challenge accepted.
And the one word that I came
up with was learn, right?
Because like you, what I was
trying to get across is that
this impacts everyone, right?
And what was kind of
strange and odd to me.
Is that we always talk about
these, uh, going back to the soft
skills, the five Cs of humanity
that AI doesn't replace, right?
From, uh, creativity to critical
thinking, to communication,
collaboration, curiosity.
And I would say to folks, I say as
marketers, you, you should innately
have those qualities, right?
But what was concerning to me, I was in
those room, there was like 70 to a hundred
people, I can't remember exact number.
And there was such a large percentage
that weren't really leaning into AI yet.
This was two months ago.
And so I said on the panel, I say,
I've talked to a lot of folks, and
they said, Hey, what is your hot
take or your spicy comment, Greg?
And I said, look, you can't wait.
You know?
'cause a lot of people were saying,
well, it is focused on that, or
this group is focused on that.
I said, you can't wait.
I said, you need to be in
control of your own destiny.
I said, you need to be out there and be on
the forefront of this because, you know,
we talked about this a little bit earlier.
There's so many tools out there,
and we're in this era of what I
would describe as taste and trust.
Mm-hmm.
Because there's gonna
be thousands of tools.
Yes.
You right.
And you're not gonna switch.
I've listened to you on other podcasts.
Talk about why you love your tech stack,
and you described it as your tech stack.
Yes.
And I think that more people need to
understand what is your tech stack?
What is your, and it's
not just your tech stack.
What is your workflow look like?
Where do you fill in,
depending on your role?
So it was more of a comment, but I really
appreciated that the, the sentiment there,
because I've fundamentally believed it.
But it goes back to the cores.
We have to learn.
These technologies are moving so
fast and a lot of folks in our
industry, you know, historically,
they only had to kind of reinvent
themselves every five to 10 years.
Now these things are changing
every five to to 10 weeks, right?
Yes.
And every time I take a new course,
I learn something new or different.
And so one thing, um, when you
were on that uh, uh, GTM AI
podcast, that reminds me of, uh.
People are talking about, it's more,
uh, it's less about Terminator and
more about Ironman suits, right?
In Jarvis, yes.
Like we're creating these Ironman suits
where people, you know, you're a craftsman
or you know you're an expert, right?
And so if we can move it from stop
thinking Terminator to saying, I have
this Ironman suit that's gonna help me
do all the things I wanna do, but I'm
still the human inside of this thing.
Right.
Ashley Gross: Absolutely.
And I think everything you just
summarized, if I was asked that question,
I think my one word would be intention.
Because without intention,
you're not doing anything.
You're not driving any change.
And I think that's the biggest.
Barrier that a lot of people face is
they see, I mean the news is saturated,
oversaturated at this point with like
all these different tools and use cases
and you know, companies laying off
employees here and replacing them with ai.
But then over here companies are using
AI plus humans and making way more money.
So there's just a lot of news and no.
General intention and every single
human being is different, and I think
it's so much easier for us to go on
autopilot and just wake up every day
and do the same thing over and over
again because we always do it this way.
Instead of just setting an
intention, where do we wanna be
in three to five years from now?
What does that look like?
What do you want your lifestyle to be?
Where do you wanna geographically sit?
What do you want your
family dynamic to be like?
Write that down and set that
intention, and then figure out how
you can use this technology to get
that three year plan in one year.
Or in less time, like figure out
what that looks like for all of you.
My intention back then was to spend
time with my son and be a new mom and
be able to balance work with a newborn
because I couldn't take time off.
If it wasn't for that intention,
I would've very much probably
stayed on autopilot because of the
convenience of, well, let's just keep
doing it this way because it works.
Sure, we could try to experiment
a different way, but we
don't know if that works.
We don't know the ROI yet for that,
so why not just stay on autopilot?
So set the intention for yourself,
because at the end of the
day, this is not a relay race.
So if you're spending all your time
looking over here and looking over here
and listening to how other people are.
Maybe using AI or maybe just posting
about it on LinkedIn and you're not
actually seeing them use ai, you're
not doing anything for yourself.
Erica Rooney: So I gotta
know, 'cause I'm nosy.
What is your tech stack that you use
and what do you use those tools for?
Ashley Gross: Yes, so a lot of my
tech stack, I do 60 day audits.
So I would say that the only
permanent staples that have been
in my tech stock for a year.
Plus our Chad CBT Claude Perplexity.
And I would say like the use cases for
cha GPT or personalization, like I am
swimming in Cha g PT every single day.
So is my team, um, mostly from a
creative perspective because my
creative workflow is I love to
lead myself voice, audio notes.
Like when I'm walking outside with my
son at night, like that's when I get my
ideas off the ground or plan my talk track
for a conference or plan my next course.
So I will take those audio notes
and upload them to chat GPT and
have them reformat it into content,
into um, social media posts, into
course outlines, and then I'll even.
Go so far as to bring the app
up and have conversations with
chat GPT where I role play it.
So I'm taking my original ideas and like
brain dumping them into my voice memo
notes, putting them into chat, GPT to free
reformat, and then questioning and having
like a strategic session back and forth.
Why did you say this?
Why do you think this could be improved?
Why are you asking these
questions if you're this
stakeholder for this talk track?
Um, 'cause I don't wanna become so
dependent on this technology that
I lose me, if that makes sense.
So it's important for me to.
Not just stay human in the loop,
but keep my creative process that I
started with and then figure out like
how to make it better, but why they're
saying it's gonna be better this way.
Because like, I want that
type of ongoing learning.
Um, and then with Claude, I'm using it
to consistently help me code better.
So like C Sharp is not something
that I had ever touched prior
to, like a year and a half ago.
Like, it's just not my jam.
I'm, I'm a Python girl
through and through.
Um, so I will use Claude and it will
help me find errors in code lines.
Because like already learning
something new and learning how to
code a certain way is enough for me.
Um, so like going through my code
and finding like the line with the
air so I don't have to like scan
through it and spend hours is the
reason I use Claude, um, perplexity.
I create content.
At the end of the day.
I have an agency.
I create courses, but like I'm a content
creator, like I gotta push content out.
So I wanna know how quickly I can find
value and resources when users are asking
questions because AI engine optimization
is what people are using more than Google.
They want to.
Ask a question into an AI engine,
see the results, and even maybe
purchase right from that ai.
Like you can go research an espresso
machine on Cha gt, have it pull and
rank a bunch of different ones, and then
purchase it without ever leaving cha GPT.
I wanna know what my customers
are doing and asking for so that
I can make sure that my content is
ranking high and providing value,
and they don't have to scroll.
Um, the other tools in my tech stack
that are always permanent, I would say,
are a mix of automation and agent tools.
So I love NAN, um, for myself personally.
And then my agent tools that
I love to use are a little bit
of Lindy, which is an AI agent.
Um, but then also a lot of the
tools that I'm coding on my own.
And then the rest of that is just
a scrappy tech stack, because when
I work with enterprises, they have,
you know, either Google or Microsoft.
So I'm playing with their
tools that they like.
So for me, I like to keep it
super simple, super scrappy.
I don't need a whole
tech stack for my team.
Greg Boone: I could tell, like, uh,
on, so I listened to, you know, like
I said, so I, I knew I was taking
notes to see like, all right, there's
what you said in October and now
knows what you're saying right now.
And that's part of it.
Like some of it has changed a little bit.
I noticed even on your, um, your site
and we'll, we'll talk about that.
Um, or will we get, you know, in
show notes, but, you know, I could
tell right away that you use N eight
N because I saw a workflow Yes.
On the, on the site.
When I scroll down, I was like, okay.
I know one of the things I heard
you talk a little bit about, um.
Agents and ag workflow before I've used
like, uh, crew, AI and, um, you know,
l chain, some other things that we are
looking at some MCP type things, right.
And going a little bit deeper, but I try
not to, going back to my, my fundamental
belief is that I try not to go too
deep with some of those things that
you can automate, uh, down the road.
Because I just also understand
that a lot of people aren't even,
they're not doing the basic right.
Right.
And so we talk about fear
and and shock, right?
And we start introducing these very,
you and I know that they're not
as complex as they sound, right.
But to other folks who are like,
Hey man, I just want to understand
how to use Chatt PT or Claude
or Perplexity or others, right?
Right.
I use Chatt PT quite a bit and um.
You know, which I think brings us
to a great segment here, Erica.
What's our segment we're gonna do next?
Erica Rooney: This is our favorite
thing on all the podcasts.
So if you haven't listed, you're
gonna be caught by surprise,
but it's called Last Chat.
And so this is our game.
You've gotta go into your
chat bot and you have to share
your last chat with us, okay?
We've had everything from mental
health breakdowns to perimenopause
to what LM you're using.
So all the things, but don't worry.
We will also get, we
Ashley Gross: also gonna share,
Erica Rooney: we will also
get vulnerable with you.
Ashley Gross: Okay.
Let's do it.
Erica Rooney: What I will say is, so I
just got back from an HR conference and I
love that Chad, GBT literally titled this.
This for me, HR Unfiltered.
Got you.
But what I wanted was I wanted some
help to make something a little
bit more punchier in my keynote.
And so I was plugging in different options
and I was asking for spicier versions
and I mean chat, GBT delivered and then
even said, Hey, do you want me to format
this for a closing slide or do you want
me to write a LinkedIn version to keep
the conversation going after your talk?
So what I love about chat
is they have learned that.
I'm a speaker.
This is what I do.
This is how I'm usually
asking for content.
So it already knows.
And we've talked about, Greg's always
asks for monetization opportunities.
I
Greg Boone: don't know,
did I ask for that?
But it realized what I was trying to do.
It
Erica Rooney: gives him that, yes,
no matter what I do now, learn.
Yes.
But I love how it learns and I
love how it just keeps it going.
It gives me just the right
amount of emojis that I like.
I mean, it has truly become this
intuitive right hand woman for me.
Yes.
So I absolutely love it.
But what's yours?
Ashley Gross: Okay, so mine is not
professional because this morning.
I was trying to do a lot
of baking last minute.
So, um, mine is directions on how to
salvage a sourdough, um, hamburger roll
recipe because I let it sit overnight.
I know it's a little bit LaMer, but
I'm very proud of my sourdough baking.
I named my sourdough starter Clint
Yeastwood, and it's been alive for a year.
So, hey, listen, this is a
COVID thing that that has.
Kept going.
Yes.
Yes, very much so.
So I, uh, I let it sit a little
too long in the fridge, and when
I opened my fridge, it was quite
literally like spilling out.
And I was like, I am, oh boy.
I'm screwed.
I need to figure out how to salvage this.
So I was asking Chacha this morning
how to salvage it and not contain
Clint Eastwood not contained.
Greg Boone: We, we almost got through an
entire episode without making a recipe AI
Erica Rooney: reference.
Like
Greg Boone: every time we
do one right, it is like.
I call it my Diane rule.
I have a friend, Diane, that, that
hates that we talk about these things.
So if she hears this, I
was like, I tried Diane.
But it is so easy to
make that analogy right.
Um,
Erica Rooney: because
we all connect with it.
Greg Boone: We all, we all connect.
We all gotta eat right.
We all
Erica Rooney: gotta eat.
Greg Boone: All right.
So mine was, um.
Not professional, but
it was family oriented.
Right.
Okay.
So I have three kids.
They're four, six, and eight years old.
Um, right.
So they're very, uh, my oldest,
my 8-year-old is very creative
in a lot of different ways.
So I think she's gonna be an
amazing marketer someday, or Cee
o or doctor, whatever the hell she
wants to be, she's gonna be it.
Right.
And so her name is, uh, e. And, uh,
I, so I, I asked Chachi pt, she, so
Ebe wanted us, she wanted the whole
family before bedtime to come to her
room because she had set up what she
called her magical museum, right?
So she created this magical museum.
So I said, all right, as a
marketer, I need to now help her
with some of this branding, right?
So I said, uh, generate a cartoon
picture of an Afro-Latina 8-year-old
showcasing her magic museum
called e B's Magical Museum.
Right?
And so it created an image
and I'll, you know, we'll post
it or whatever later, right?
And so it created this great.
Image.
You can't see it.
Erica can see it here.
I don't know if folks can see it.
Right.
But the whole, that's amazing.
You know, and I did it in, you know,
whatever, it took three minutes.
Mm-hmm.
And so I ca so she was like,
I'm gonna go finish setting up.
I came upstairs, you know, showcase this.
She was like, when did you do that?
And I said, you're not, I
just did it just now baby.
She's like, but I just told you.
I was like, yeah, well these tools,
and the funny thing I always tell
people, your work is she's in
second grade and they're already
learning AI and they're using Canva.
So she's been creating things
in Google Slides and Canva.
So she was excited.
Now she wants it, so now that she can go
make some more stuff and iterate on it.
So I got my own marketing
workflow at home right now.
Right?
And so I was just excited about that.
So I almost forgot about
the last chat segment.
I was like, oh.
This is a good one.
She's gonna rule
Ashley Gross: the world.
She's set up for success.
I love it.
Love that.
No, that's a great,
that's a great use case.
Our dog passed, um, last Christmas, and
so we were like, what is there, like,
is there a book for four year olds that
explains this in like non weird ways?
So we asked Chare, like a nice little
story about like the dog going to heaven
and yeah, like it worked perfectly.
It helped us like navigate
a very tough conversation.
We didn't think we would
have to have that early.
And yeah, like five minutes to your
point where it's like they ask a question
and you're supposed to know, 'cause
you're mom or dad and you're like, I
need to give them something so they
don't let their imagination run wild.
Uh, so that's what we did.
Love it.
Rainbow Bridge poem.
Exactly.
Exactly.
Erica Rooney: Oh my gosh.
Well, Ashley, thank you so
much for joining us today.
I'm super excited to also be
seeing you in Boston for the ai.
Powered Women's Conference.
Y'all come see all of us.
Greg, myself, Ashley, we are all
gonna be there supporting Dr.
Felicia Newhouse.
It's going to be incredible.
Check out Ashley.
Follow her on LinkedIn,
check out her courses.
She's doing it all.
And until next time, you guys,
thank you so much for joining us.
Greg Boone: Thank you, Ashley.
Erica Rooney: Thanks for joining
us on AI, voice or victim.
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